Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: Divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles

Chemical Communications

Volumn 51, Issue 1, 2015, Pages 133-136

  Tang, Xiang Ying ^a   Zhang, Yong Sheng ^a   He, Lv ^b   Wei, Yin ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLENE 2,3 DIHYDROBENZOFURAN DERIVATIVE; 3 METHYLENE 2,3 DIHYDROINDOLE DERIVATIVE; AROMATIC COMPOUND; BENZOFURAN DERIVATIVE; CARBENE; INDOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; COORDINATION COMPOUND; METHANE; RHODIUM;

ANNULATION REACTION; ARTICLE; CATALYST; CONTROLLED STUDY; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH TEMPERATURE; HYDROGENATION; ONE POT SYNTHESIS; REACTION TIME; RING OPENING; X RAY DIFFRACTION; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BENZOFURANS; CATALYSIS; COORDINATION COMPLEXES; CYCLIZATION; INDOLES; METHANE; RHODIUM; TRIAZOLES;

EID: 84915750829     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc08343a     Document Type: Article

References (83)

1. Y. Liu M. Kubo Y. Fukuyama J. Nat. Prod. 2012 75 2152
2. T. Nagahara Y. Yokoyama K. Inamura S. Katakura S. Komoriya H. Yamaguchi T. Hara D. Argentieri W. Hagenman J. Med. Chem. 1994 37 1200
3. Z. Yang H. B. Liu C. M. Lee H. M. Chang H. N. C. Wong J. Org. Chem. 1992 57 7248
4. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970
5. R. J. Sundberg, Indoles, Academic Press, San Diego, 1996
6. R. H. Thomson, The Chemistry of Natural Products, Blackie and Son, Glasgow, 1985
7. F.-E. Chen J. Huang Chem. Rev. 2005 105 4671
8. A. Fürstner P. W. Davies J. Am. Chem. Soc. 2005 127 15024
9. I. Nakamura Y. Mizushima Y. Yamamoto J. Am. Chem. Soc. 2005 127 15022
10. D.-H. Lee K.-H. Kwon C. S. Yi J. Am. Chem. Soc. 2012 134 7325
11. T. J. Maimone S. L. Buchwald J. Am. Chem. Soc. 2012 134 7325
12. Y. Wei I. Deb N. Yoshikai J. Am. Chem. Soc. 2012 134 9098
13. S. G. Newman M. Lautens J. Am. Chem. Soc. 2010 132 11416
14. S. Wagaw B. H. Yang S. L. Buchwald J. Am. Chem. Soc. 1998 120 6621
15. M. C. Willis G. N. Brace I. P. Holmes Angew. Chem., Int. Ed. 2005 44 403
16. B. J. Stokes H. Dong B. E. Leslie A. L. Pumphrey T. G. Driver J. Am. Chem. Soc. 2007 129 7500
17. Y. Wang A. Zhang Tetrahedron 2009 65 6986
18. K. Sasaki Y. Kondo K. Maruoka Angew. Chem., Int. Ed. 2001 40 411
19. A.-L. Girard R. Lhermet C. Fressigné M. Durandetti J. Maddaluno Eur. J. Org. Chem. 2012 2895
20. M. Durandetti L. Hardou R. Lhermet M. Rouen J. Maddaluno Chem.-Eur. J. 2011 17 12773
21. S. N. Osipov N. M. Kobel'kova A. F. Kolomiets K. Pumpor B. Koksch K. Burger Synlett 2001 1287
22. Q. Liu B. Han W. Zhang L. Yang Z.-L. Liu W. Yu Synlett 2005 2248
23. B. Burns R. Grigg V. Sridharan P. Stevenson S. Sukirthalingam T. Worakun Tetrahedron Lett. 1989 30 1135
24. Y. Terada M. Arisawa A. Nishida Angew. Chem., Int. Ed. 2004 43 4063
25. M. Arisawa Y. Terada K. Takahashi M. Nakagawa A. Nishida J. Org. Chem. 2006 71 4255
26. B. Chattopadhyay V. Gevorgyan Angew. Chem., Int. Ed. 2012 51 862
27. A. V. Gulevich V. Gevorgyan Angew. Chem., Int. Ed. 2013 52 1371
28. H. M. L. Davies J. S. Alford Chem. Soc. Rev. 2014 5151
29. T. Horneff S. Chuprakov N. Chernyak V. Gevorgyan V. V. Fokin J. Am. Chem. Soc. 2008 130 14972
30. T. Miura M. Yamauchi M. Murakami Chem. Commun. 2009 1470
31. J. S. Alford H. M. L. Davies Org. Lett. 2012 14 6020
32. S. Chuprakov S. W. Kwok L. Zhang L. Lercher V. V. Fokin J. Am. Chem. Soc. 2009 131 18034
33. N. P. Grimster L. Zhang V. V. Fokin J. Am. Chem. Soc. 2010 132 2510
34. J. C. Culhane V. V. Fokin Org. Lett. 2011 13 4578
35. M. Zibinsky V. V. Fokin Org. Lett. 2011 13 4870
36. B. T. Parr H. M. L. Davies Angew. Chem., Int. Ed. 2013 52 10044
37. J. S. Alford J. E. Spangler H. M. L. Davies J. Am. Chem. Soc. 2013 135 11712
38. S. W. Kwok L. Zhang N. P. Grimster V. V. Fokin Angew. Chem., Int. Ed. 2014 53 3452
39. H. Shang Y. Wang Y. Tian J. Feng Y. Tang Angew. Chem., Int. Ed. 2014 53 5662
40. M. Zibinsky V. V. Fokin Angew. Chem., Int. Ed. 2013 52 1507
41. T. Miura T. Tanaka K. Hiraga S. G. Stewart M. Murakami J. Am. Chem. Soc. 2013 135 13652
42. B. Chattopadhyay V. Gevorgyan Org. Lett. 2011 13 3746
43. Y. Shi V. Gevorgyan Org. Lett. 2013 15 5394
44. E. E. Schultz R. Sarpong J. Am. Chem. Soc. 2013 135 4696
45. S. Chuprakov S. W. Kwok V. V. Fokin J. Am. Chem. Soc. 2013 135 4652
46. J. E. Spangler H. M. L. Davies J. Am. Chem. Soc. 2013 135 6802
47. B. T. Parr S. A. Green H. M. L. Davies J. Am. Chem. Soc. 2013 135 4716
48. Y. Xing G. Sheng J. Wang P. Lu Y. Wang Org. Lett. 2014 16 1244
49. E. E. Schultz V. N. G. Lindsay R. Sarpong Angew. Chem., Int. Ed. 2014 53 9904
50. J. S. Alford H. M. L. Davies J. Am. Chem. Soc. 2014 136 10266
51. X. Ma S. Pan H. wang W. Chen Org. Lett. 2014 16 4554
52. D. J. Lee H. S. Han J. Shin E. J. Yoo J. Am. Chem. Soc. 2014 136 11606
53. S. Rajasekar P. Anbarasan J. Org. Chem. 2014 79 8428
54. R.-Q. Ran J. He S.-D. Xiu K.-B. Wang C.-Y. Li Org. Lett. 2014 16 3704
55. F. Medina C. Besnard J. Lacour Org. Lett. 2014 16 3232
56. C.-E. Kim S. Park D. Eom B. Seo P. H. Lee Org. Lett. 2014 16 1900
57. T. Miura T. Biyajima T. Fujii M. Murakami J. Am. Chem. Soc. 2012 134 194
58. T. Miura T. Tanaka T. Biyajima A. Yada M. Murakami Angew. Chem., Int. Ed. 2013 52 3883
59. T. Miura T. Tanaka A. Yada M. Murakami Chem. Lett. 2013 42 1308
60. S. Chuprakov B. T. Worrell N. Selander R. K. Sit V. V. Fokin J. Am. Chem. Soc. 2014 136 195
61. S. Chuprakov J. A. Malik M. Zibinsky V. V. Fokin J. Am. Chem. Soc. 2011 133 10352
62. J.-M. Yang C.-Z. Zhu X.-Y. Tang M. Shi Angew. Chem., Int. Ed. 2014 53 5142
63. D. Yadagiri P. Anbarasan Org. Lett. 2014 16 2510
64. N. Selander B. T. Worrell S. Chuprakov S. Velaparthi V. V Fokin J. Am. Chem. Soc. 2012 134 14670
65. N. Selander V. V. Fokin J. Am. Chem. Soc. 2012 134 2477
66. T. Miura Y. Funakoshi M. Morimoto T. Biyajima M. Murakami J. Am. Chem. Soc. 2012 134 17440
67. R. Liu M. Zhang G. Winston-McPherson W. Tang Chem. Commun. 2013 49 4376
68. K. Chen Z.-Z. Zhu Y.-S. Zhang X.-Y. Tang M. Shi Angew. Chem., Int. Ed. 2014 53 6645
69. T. Miura Y. Funakoshi T. Tanaka M. Murakami Org. Lett. 2014 16 2760
70. T. Miura T. Nakamuro K. Hiraga M. Murakami Chem. Commun. 2014 50 10474
71. A. Boyer Org. Lett. 2014 16 1660
72. J. E. Hein V. V. Fokin Chem. Soc. Rev. 2010 39 1302
73. B. T. Worrell J. A. Malik V. V. Fokin Science 2013 340 457
74. X. Lu Top. Catal. 2005 35 73
75. Z. Wang X. Lu J. Org. Chem. 1996 61 2254
76. Z. Wang Z. Zhang X. Lu Organometallics 2000 19 775
77. B. Rajagopal C.-H. Chou C.-C. Chung P.-C. Lin Org. Lett. 2014 16 3752
78. D < 1, ∼0.8-0.9), see: L. Melander, Isotope Effect on Reaction Rates, Ronald Press, New York, 1960, pp. 107-123
79. E. V. Anslyn and D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, 2006, p. 428
80. S. Piacente C. Pizza W. Oleszek Phytochem. Rev. 2005 4 177
81. C. Balestrieri F. Felice S. Piacente C. Pizza P. Montoro W. Oleszek V. Visciano M. L. Balestrieri Biochem. Pharmacol. 2006 71 1479
82. S. Marzocco S. Piacente C. Pizza W. Oleszek A. Stochmal A. Pinto R. Sorrentino G. Autore Life Sci. 2004 75 1491
83. E. M. Wenzig W. Oleszek A. Stochmal O. Kunert R. Bauer J. Agric. Food Chem. 2008 56 8885